This chapter investigates the sustainability strategies formulated in relation to circular economy (CE) practices, and the digital technologies supporting them, in the clothing retail sector in Romania. The study is motivated by the high impact on consumer preferences of large clothing retailers through their physical stores. The research adopts a triangulated methodology, with data being collected through a combination of field research, content analysis, and website/app functionality investigation, in 15 retailers that have a significant presence in Romania and worldwide. The data was analysed using an original evaluation sheet including 23 criteria. The findings indicate that major clothing retailers in Romania apply the CE principles in a very selective way. Some practices (such as labelling recycled fibers/materials for individual items) are present in most stores, while others are absent in most cases (e.g., returning used/old clothes for shopping credit). There are significant differences between companies’ CE practices in clothing retail in Romania. Regarding the use of digital technologies to support CE practices, the findings indicate certain aspects that can be improved upon by the brands included in the sample, such as the availability of targeted loyalty programs, apps, surveys, and social media messages.